My boyfriend keeps borrowing my money and NEVER pays me

My boyfriend keeps borrowing my money and NEVER pays me back

dear Jane,

My oldest friend is always in financial difficulties and has asked me for money (again). She always promises to pay me back, but I’ve never seen a penny.

I’ve always stepped in to help, but I’ve just found out from another friend that my struggling friend booked a luxury cruise for the two of them and asked her not to tell me.

I am shocked and hurt and feel betrayed. She’s just asked for another “loan,” but she’s apparently using the money to secretly live a lavish lifestyle.

What can I do?

love getting poorer

Dear Jane, My oldest friend is always in financial difficulties and has asked me for money (again). She always promises to pay me back, but I’ve never seen a dime, despite the fact that she keeps making lavish trips

love increasingly poor,

My grandfather always quoted Shakespeare: ‘Be neither a borrower nor a lender.’

In other words, don’t borrow or lend money. What he meant was not that you should never help a friend in need, as you have done countless times, but that if you want to help financially, you should consider it a gift and not a loan.

Too many friendships have been ruined by money, and it’s fair to assume that someone who’s repeatedly got themselves into financial trouble might have a hard time repaying you. If you are willing and able to help them financially, the only way forward is to drop all expectations that you will be repaid.

Years ago I had a friend who was going through a terrible time and I knew the financial stress she was under was tremendous. I’ve never quite understood why she never had any money but sent her a large amount – I was particularly flushed at the time – which I suspected would get her out of the hole.

The international best-selling author offers wise advice on the hottest topics of  readers in her weekly column Dear Jane Agony Tante

The international best-selling author offers wise advice on the hottest topics of readers in her weekly column Dear Jane Agony Tante

The first thing she said after tears of relief was that she would pay me back, but I never expected her to do it.

In my mind it was a gift. Over the years I’ve seen her spend money lavishly on things I wouldn’t spend money on in that position, but that’s her choice, just as it was my choice to give her money with no strings attached. I realized that it wasn’t my job to tell her where to spend her money, and if she spent it on designer handbags, I had to be okay with that.

Despite this, I decided that I would no longer lend money to this particular friend and would be happy to support her in other ways.

That’s the problem with giving money. If it’s a gift, they can do whatever they want with it.

The bigger problem is that your friend asks someone else to keep the cruise a secret. She knows she’s being judged, but how much better would it have been if she’d been transparent?

Who knows, if she came up to you and said, “I haven’t had a vacation in years, I’m exhausted, I have no money and I have the opportunity to go on a cruise, is there anything you can do to help?” Me?’ maybe you would have said yes, pleased to be able to help her.

That she is trying to hide this is deceptive. I suggest you sit down with her and just say this: if she had been honest you would have had a choice, but now you feel betrayed by what she did. See what she has to say, but I’m not sure a friendship can or should survive that kind of betrayal.

dear Jane,

Last year I divorced (amicably) my husband of 26 years; There was nothing “wrong” about our relationship per se, but over the years we grew apart and the spark that we were fortunate to enjoy for so long eventually faded to nothing.

At the encouragement of my friends, I joined a few dating apps – just to see what’s out there – and a few months ago I finally hooked up with an amazing, handsome man… who happens to be 18 years younger than me.

In many ways it was wonderful. He’s thoughtful, passionate, energetic and he’s rekindled my own sense of adventure. But at 49, I find it incredibly difficult to embrace his lifestyle.

I don’t want to party late into the wee hours with a group of 30s in bars, and I certainly don’t find the prospect of a “10-person budget ski trip” alluring—but I don’t want him to think I do either be old and boring.

Is there any way I can prove that age really is just a number? Or will I only date older men for the rest of my life?


Aging shamefully

Dear shameful aging,

It sounds like you’re already starting to think this might not be the relationship for you, and I’m guessing, given your concerns, that might take its course.

However, I don’t think for a second that you’re stuck with older men. In fact, as far as I’m concerned, after you’ve almost hit the best decade of your life, you can decide exactly what kind of relationship you want and what works for you.

Dear Jane’s Sunday service

Say what you mean, mean what you say, don’t say it like that

Many years ago I heard this saying and it changed my life. So often we’re afraid to be honest, we worry that people won’t like us, we worry that they might get angry.

When we are honest and say things calmly and kindly, it is much easier for people to listen to us.

Whether it’s saying I love you but I can’t lend you any more money, or I love being with you but a cheap ski trip isn’t something I’d enjoy, if we’re clear and friendly it won’t just heard it’s better for us and infinitely better than weaving a web of lies.

One of my best friends has been dating a wonderful man for five years and they are pretty sure they will be together for life.

Each of them has their own house, and although they spend some evenings and nights together, at least half the week she is allowed to go to her house, change into her softest pajamas, and climb into bed with a cup of tea, a stack of magazines, and a cat. What she calls “heaven”.

There are so many joys of aging – comfort in our skin, the ability to say no, choosing what we will and will not tolerate in our lives. We care less about what others think of us and realize that we no longer have to please people, that in fact, if we’re going to be in bed by nine o’clock every night, we have every right to forego bar hopping and late night parties.

Every woman I know over 45 works to perfect their Irish exit (leaving an event very quietly, without saying goodbye and ideally unnoticed). My never again list includes futons, white wine wrappers, and giant cruise ships.

As for Old and Boring, check out style icon Iris Apfel – she’s 101 years old, as stylish as ever and still rolling out new lines! I dare anyone to call them old and boring.

This is less about age and more about stage. It sounds like you are at a different stage in your life and ultimately want to find someone who shares similar interests and sensibilities.

In the meantime, stop worrying about what others think of you for aging shamefully because you have earned the right to live your life the way you want, regardless of what others think.